3-(1,1-Dimethyl-2-propen-1-yl)-7-hydroxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-2-one

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  • Identifiers

    CAS number
    21316-80-3

    Molecular formula
    C19H22O3

    SMILES
    CC(=CCC1=C(C=C2C(=C1)C=C(C(=O)O2)C(C)(C)C=C)O)C

    Safety labels

  • Odor profile

    Fragrance
    Herbal 47.53%
    Spicy 44.28%
    Woody 42.48%
    Fruity 41.83%
    Phenolic 36.22%
    Dry 33.65%
    Citrus 29.06%
    Mint 26.49%
    Leathery 25.42%
    Sweet 25.18%

     

    Flavor
    Bitter 59.15%
    Herbal 29.41%
    Woody 27.43%
    Camphor 20.22%
    Cedarleaf 20.03%
    Heather 19.67%
    Lovage 19.63%
    Broom 19.53%
    Parsley 19.35%
    Genet 19.34%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    5.4

    pKa est.
    8.17 (weak base)

    Molecular weight
    298.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    575°C

    Melting point expt.

    • 166 - 168 °C

    Flash point

    • 180.71 ˚C est.

  • Synonyms

    • 21316-80-3
    • RefChem:1066349
    • 3-(1,1-Dimethyl-2-propen-1-yl)-7-hydroxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-2-one
    • Gravelliferone
    • CHEMBL5177258
    • 7-hydroxy-3-(2-methylbut-3-en-2-yl)-6-(3-methylbut-2-enyl)chromen-2-one
    • 2H-1-Benzopyran-2-one, 3-(1,1-dimethyl-2-propen-1-yl)-7-hydroxy-6-(3-methyl-2-buten-1-yl)-
    • Gravelliferone methyl ether
    • orb1991430
    • SCHEMBL29376680
    • DTXSID90556369
    • CHEBI:174840
    • BDBM50591783
    • AKOS040735342
    • 7-hydroxy-6-(3-methylbut-2-en-1-yl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one
    • NS00094854
    • 3-(1,1-Dimethylallyl)-7-hydroxy-6-(3-methyl-2-butenyl)coumarin, 8CI
    • 3-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9CI
    • 7-Hydroxy-3-(2-methylbut-3-en-2-yl)-6-(3-methylbut-2-en-1-yl)-2H-1-benzopyran-2-one
    • 21316-80-3

  • Applications

    3-(1,1-Dimethyl-2-propen-1-yl)-7-hydroxy-6-(3-methyl-2-buten-1-yl)-2H-1-benzopyran-2-one (CAS 21316-80-3) is a prenylated coumarin derivative with applications as a fragrance ingredient and odorant in perfumery and cosmetics, where its coumarin-type aroma can contribute to formulation profiles; it may also be evaluated for flavor/aroma applications in select food or beverage systems under appropriate regulatory approvals. The compound serves as an organic synthesis intermediate for access to more complex benzopyranone derivatives in pharmaceutical and agrochemical research and development, and can function as a building block in specialty polymers or coatings research under applicable regulations. In household products, it can be employed as a fragrance additive to impart aroma in cleaners and detergents, subject to formulation limits and local rules.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 85.71
    methanol 62.25
    isopropanol 65.56
    water 0.0
    ethyl acetate 122.56
    n-propanol 103.8
    acetone 135.24
    n-butanol 78.85
    acetonitrile 33.01
    DMF 603.81
    toluene 72.17
    isobutanol 72.54
    1,4-dioxane 185.93
    methyl acetate 134.09
    THF 562.41
    2-butanone 270.91
    n-pentanol 61.25
    sec-butanol 93.11
    n-hexane 0.98
    ethylene glycol 5.24
    NMP 264.74
    cyclohexane 1.2
    DMSO 211.89
    n-butyl acetate 114.71
    n-octanol 20.44
    chloroform 172.59
    n-propyl acetate 94.87
    acetic acid 59.32
    dichloromethane 169.27
    cyclohexanone 222.19
    propylene glycol 25.89
    isopropyl acetate 90.47
    DMAc 572.93
    2-ethoxyethanol 142.85
    isopentanol 80.84
    n-heptane 0.81
    ethyl formate 47.15
    1,2-dichloroethane 140.32
    n-hexanol 70.14
    2-methoxyethanol 262.04
    isobutyl acetate 73.47
    tetrachloromethane 4.92
    n-pentyl acetate 72.85
    transcutol 597.99
    n-heptanol 31.39
    ethylbenzene 27.64
    MIBK 94.72
    2-propoxyethanol 228.98
    tert-butanol 94.41
    MTBE 91.46
    2-butoxyethanol 105.52
    propionic acid 55.7
    o-xylene 26.15
    formic acid 13.77
    diethyl ether 67.27
    m-xylene 35.9
    p-xylene 37.77
    chlorobenzene 68.46
    dimethyl carbonate 53.21
    n-octane 0.54
    formamide 45.42
    cyclopentanone 323.08
    2-pentanone 163.46
    anisole 97.01
    cyclopentyl methyl ether 134.4
    gamma-butyrolactone 242.29
    1-methoxy-2-propanol 231.07
    pyridine 263.49
    3-pentanone 106.31
    furfural 175.18
    n-dodecane 0.62
    diethylene glycol 93.93
    diisopropyl ether 15.75
    tert-amyl alcohol 103.02
    acetylacetone 158.34
    n-hexadecane 0.75
    acetophenone 88.96
    methyl propionate 132.81
    isopentyl acetate 124.53
    trichloroethylene 329.95
    n-nonanol 23.37
    cyclohexanol 55.53
    benzyl alcohol 80.5
    2-ethylhexanol 38.02
    isooctanol 29.12
    dipropyl ether 37.08
    1,2-dichlorobenzene 52.25
    ethyl lactate 42.95
    propylene carbonate 99.46
    n-methylformamide 122.34
    2-pentanol 51.97
    n-pentane 0.83
    1-propoxy-2-propanol 154.32
    1-methoxy-2-propyl acetate 171.89
    2-(2-methoxypropoxy) propanol 125.65
    mesitylene 13.0
    ε-caprolactone 192.35
    p-cymene 16.28
    epichlorohydrin 471.94
    1,1,1-trichloroethane 70.42
    2-aminoethanol 32.89
    morpholine-4-carbaldehyde 345.21
    sulfolane 235.86
    2,2,4-trimethylpentane 1.4
    2-methyltetrahydrofuran 243.14
    n-hexyl acetate 79.9
    isooctane 1.1
    2-(2-butoxyethoxy)ethanol 182.0
    sec-butyl acetate 77.68
    tert-butyl acetate 115.58
    decalin 1.72
    glycerin 35.58
    diglyme 314.23
    acrylic acid 42.94
    isopropyl myristate 28.66
    n-butyric acid 102.13
    acetyl acetate 48.88
    di(2-ethylhexyl) phthalate 35.3
    ethyl propionate 77.82
    nitromethane 152.7
    1,2-diethoxyethane 155.65
    benzonitrile 66.66
    trioctyl phosphate 21.57
    1-bromopropane 59.84
    gamma-valerolactone 463.62
    n-decanol 16.95
    triethyl phosphate 31.12
    4-methyl-2-pentanol 36.86
    propionitrile 50.14
    vinylene carbonate 87.52
    1,1,2-trichlorotrifluoroethane 157.2
    DMS 87.17
    cumene 17.1
    2-octanol 21.5
    2-hexanone 113.57
    octyl acetate 38.3
    limonene 21.61
    1,2-dimethoxyethane 254.07
    ethyl orthosilicate 32.29
    tributyl phosphate 28.82
    diacetone alcohol 169.99
    N,N-dimethylaniline 60.71
    acrylonitrile 72.51
    aniline 96.11
    1,3-propanediol 73.49
    bromobenzene 63.51
    dibromomethane 78.02
    1,1,2,2-tetrachloroethane 237.15
    2-methyl-cyclohexyl acetate 65.2
    tetrabutyl urea 43.03
    diisobutyl methanol 22.04
    2-phenylethanol 94.38
    styrene 32.76
    dioctyl adipate 48.8
    dimethyl sulfate 79.55
    ethyl butyrate 64.66
    methyl lactate 59.6
    butyl lactate 66.66
    diethyl carbonate 36.83
    propanediol butyl ether 86.38
    triethyl orthoformate 47.87
    p-tert-butyltoluene 16.84
    methyl 4-tert-butylbenzoate 80.43
    morpholine 384.65
    tert-butylamine 36.19
    n-dodecanol 11.79
    dimethoxymethane 261.16
    ethylene carbonate 65.78
    cyrene 94.62
    2-ethoxyethyl acetate 134.03
    2-ethylhexyl acetate 88.85
    1,2,4-trichlorobenzene 68.17
    4-methylpyridine 253.32
    dibutyl ether 32.2
    2,6-dimethyl-4-heptanol 22.04
    DEF 205.23
    dimethyl isosorbide 218.52
    tetrachloroethylene 80.3
    eugenol 88.52
    triacetin 82.7
    span 80 91.22
    1,4-butanediol 19.27
    1,1-dichloroethane 105.23
    2-methyl-1-pentanol 72.52
    methyl formate 70.8
    2-methyl-1-butanol 82.08
    n-decane 1.03
    butyronitrile 57.69
    3,7-dimethyl-1-octanol 33.9
    1-chlorooctane 9.83
    1-chlorotetradecane 4.03
    n-nonane 0.78
    undecane 0.79
    tert-butylcyclohexane 2.05
    cyclooctane 0.41
    cyclopentanol 70.16
    tetrahydropyran 188.28
    tert-amyl methyl ether 71.98
    2,5,8-trioxanonane 193.3
    1-hexene 12.49
    2-isopropoxyethanol 111.31
    2,2,2-trifluoroethanol 13.2
    methyl butyrate 117.35

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction